Experience isn’t something that can be easily taught. We can try to share our experiences and hope that others learn from them, but ultimately, it takes experiences to truly learn. For this reason, it can be difficult for women to maintain close friendships with men as they get older. It’s not only difficult because we’re conditioned to view men as romantic interests (although that may be a factor for some of us), but because men simply don’t understand female experiences the way other women do. Even for men who want to learn, it can be exhausting as a woman to constantly explain what seems like second nature to us.

As someone with a decent amount of male friends, I’ve had enough trial and error to weather even the most oblivious guy. It’s not necessarily our job to enlighten men on Feminism 101, but if he’s willing to learn and you’re willing to teach, here are some ways to make the whole process easier:

The More the Merrier

Don’t do it alone! Any respectable twenty-something year old man should have more than one female friend. Split up the emotional labor and gain strength and credibility in numbers. You don’t have to gang up on him or hold an intervention in order to have an effective, collaborative conversation. Any man is more likely to take your experiences seriously if you show him it’s not just a ‘you thing,’ but applies to a variety of women. Personal essays and even fiction work (‘Cat Person’ from The New Yorker is a good example) can also add voices to the room that may not physically be there. Furthermore, including multiple women will open him up to an even greater range of experiences in the female community, instead of peddling the misconception that women are a monolith.

Use Concrete Examples

When advocating for your humanity, it’s best to speak using clear, concrete examples instead of general feelings. Men can often misinterpret emotional investment as bias, and without ‘proof’ to back yourself up, a male friend may be less receptive to what you’re trying to convey. Men who have spent a lot of time on the Internet and/or writing research papers may be inclined to request sources to back up any statement you make. It may be helpful to have some on hand (Teen Vogue, Them, and Planned Parenthood all have useful articles about femininity and sexuality), but also remind him that repeated, lived experience can be a valuable educational tool. If you get stung by a jellyfish, you don’t need to pull up a website confirming that jellyfish have stingers.

Hold Him Responsible for His Friends

We are not all our brother’s keeper. Yet, if this article is any proof, men often listen to other men more readily than they listen to women. Once you’ve educated one man, release him back into the wild, hopefully ready to teach his friends everything you just taught him about women. The best way to combat social ills, such as rape culture, is to infiltrate knowledge from within. We may not (yet) live in a world where men talk about feminist social theory in the locker room, but a some men genuinely do want to better themselves and how they treat women. The more they talk to their friends, the less work you have to do for them. Believe it or not, I have male friends who regularly approach other men about their online dating habits, and those conversations lead to increased awareness and better Tinder etiquette. Sometimes, two men do make a right.

Don’t Paint Him as the Villain

Some men take feminist issues as a personal affront. While that may reflect more on him than you, don’t feed into this reaction by attacking him unjustifiably. If he needs to be held accountable for any negative actions, go ahead. Otherwise, keep messages applicable yet general if he genuinely hasn’t done anything wrong. Use phrases like 'It annoys me when men….' instead of throwaway lines like 'Men are so annoying.' Those lines are totally acceptable for personal venting, but they aren’t the most constructive for bridge-building discussion.

Don’t Talk Down to Him

While it’s true that men are blissfully unaware of a lot of the struggles women face, no man should be entirely in the dark about basic concepts, especially in today’s internet-based culture. You’ll end up having a more productive conversation if you aren’t afraid to tackle more complex issues. ‘Complex’ also doesn’t have to mean heavy! Microaggressions are just as important to learn from and correct as more serious and labor-intensive topics. Even if it turns out he’s still on square one of feminist understanding, be patient with him and yourself. Everyone experiences this learning curve at one point or another.

When advocating for your humanity, it’s best to speak with clear, concrete examples instead of general feelings.

Take Time for Yourself

Again, it’s not your job to explain anything you don’t want to! Don’t be afraid to link your male friend a personal essay and call it a day. Heck, even link him this article if you want. Heavier topics can even compromise your own mental health, causing you to relive moments you’d rather not dwell upon. Plenty of women have written about and documented similar, all-too-common experiences that you can recommend to your male friend. (I’m personally a fan of Ella Dawson’s essays about female sexuality.) ‘Femmsplaining’ can be exhausting, even if your male friend is receptive. If he’s not receptive, well, that brings me to the next tip:

Cut Him Off (If You Need To)

Sometimes, men just don’t get it. Or they don’t want to get it. You aren’t a miracle worker; you don’t have to turn every man you associate with into a perfect feminist. Sometimes, your male friend may be an irreparable negative presence in your life, completely unwilling to unlearn sexist behavior. This resistance in no way reflects poorly on you. Don’t be afraid to cut men out of your life if they continue to uphold harmful beliefs and practices. Maybe one of his male friends or a life-changing experience can get through to him, but ultimately, his education isn’t your responsibility.

Unlearning implicit behavior can be difficult for anyone. It’s so very possible to have fulfilling friendships with men, keeping in mind that their life experiences may not render them as naturally understanding of female realities. Ideally, we should befriend people who support or share our main values — these tips are mostly meant for men in need of epistemic fine-tuning, not raging chauvinists. Ultimately, we’re all human beings, and diversity in experiences is what enriches our friendships to begin with.